HCID 18400181, compound → HCID 15390788, compound

HRID 1019181Notes

Reaction equation

HRID 1019181 reaction equation
C1C=C[NH+]=CC=1.[O-:7][Cr](Cl)(=O)=O.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2(O)[CH2:24][CH2:23][CH:22]=[C:21]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>C(Cl)Cl.CCOCC>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:21]2[C:22](=[O:7])[CH2:23][CH2:24][C:20]=2[C:17]2[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 18400181HCID 18400181, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15390788HCID 15390788, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of PCC (4.5 g, 20.9 mmol) and 10 g of anhydrous 4 Å molecular sieves in 150 mL of CH2Cl2 was added a solution of 2.2 g (7.3 mmol) of 1-(4-(methylthio)phenyl)-2-(4-fluorophenyl)-2-cyclopenten-1-ol in 20 mL CH2Cl2. The mixture was stirred for 1 h at r.t. and then diluted with 300 mL of Et2O. After filtration and concentration, the residue was flash chromatographed with 2:1 hexane/EtOAc to give 1.5 g of the title product. 1H NMR (CDCl3) d 2.45 (3H, s), 2.68 (2H, m), 3.00 (2H, m), 7.02 (2H, J=8.6 Hz, t), 7.11 (2H, J=8.6 Hz, d), 7.15-7.23 (4H, m).

Workup

  1. filtrationAfter filtration and concentration
  2. customchromatographed with 2:1 hexane/EtOAc

Sources & evidence

ORD record
ord-88e69dad28a541cd9beaba31edbe20ce
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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